78960-85-7Relevant academic research and scientific papers
Perfluoroalkyl and -aryl Zinc Ate Complexes: Generation, Reactivity, and Synthetic Application
Wang, Xuan,Hirano, Keiichi,Kurauchi, Daisuke,Kato, Hisano,Toriumi, Naoyuki,Takita, Ryo,Uchiyama, Masanobu
, p. 10993 - 10996 (2015/11/10)
A combination of dimethylzinc, perfluoroalkyl iodide, and LiCl afforded a new type of perfluoroalkyl (RF) zinc ate complex. These complexes show much greater thermal stability than conventional perfluorinated metal species, such as RF-lithium species and Grignard reagents, and they can be used at room temperature or higher. The results of DFT calculations on the origin of the enhanced stability are reported and the synthetic utility of RF-zincate complexes is demonstrated. The magnificent ate: A combination of dimethylzinc, perfluoroalkyl iodide, and LiCl afforded a new type of perfluoroalkyl (RF) zinc ate complex. These complexes show greater thermal stability than conventional perfluorinated metal species and they can be used at room temperature or higher. The results of DFT calculations on the origin of the enhanced stability are reported and the synthetic utility of RF-zincate complexes is demonstrated.
Oxidation of Fluoroalkyl-Substituted Carbinols by the Dess-Martin Reagent
Linderman, Russell J.,Graves, David M.
, p. 661 - 668 (2007/10/02)
The efficient oxidation of mono-, di-, tri-, and perfluoroalkyl-substituted carbinols has been accommplished by the Dess-Martin periodinane oxidant.A variety of functional groups are compatible with the oxidation procedure.Monitoring the oxidation by 19F NMR indicated that a discreet periodinane intermediate is formed during the course of the reaction.Nonnucleophilic or sterically encumbered α-thiofluoro carbinols were readily oxidized; however, a nucleophilic α-thio-substituted trifluoromethyl carbinol was not.A tert-butyl alcohol modified periodinane oxidant was ultimately employed to achieve oxidation in this example.
Ultrasound-Promoted Selective Perfluoroalkylation on the Desired Position of Organic Molecules
Kitazume, Tomoya,Ishikawa, Nobuo
, p. 5186 - 5191 (2007/10/02)
Perfluoroalkylzinc iodides or bromides wich were prepared from perfluoroalkyl iodides or bromides and zinc powder in N,N-dimethylformamide or tetrahydrofuran with ultrasonic irradiation were found to behave as potential perfluoroalkylating reagents for the preparation of a wide variety of perfluoroalkylated compounds.Especially, the ultrasound-promoted asymmetric induction with perfluoroalkyl group on the asymmetrical carbon was achieved by the reaction of perfluoroalkyl halides with optically active enamines in the presence of zinc powder and a catalytic amount of dichlorobis(?-cyclopentadienyl)titanium.
PALLADIUM AND NICKEL-CATALYZED PERFLUOROALKYLATION OF ALDEHYDES USING ZINC AND PERFLUOROALKYL HALIDES
O'Reilly, Neil J.,Maruta, Masamichi,Ishikawa, Nobuo
, p. 517 - 520 (2007/10/02)
A room temperature method for the conversion of perfluoroalkyl iodides to α-perfluoroalkyl carbinols under Pd or Ni catalysis is reported.The use of trifluoromethyl bromide provides an economical procedure for trifluoromethyl substituted carbinols.
